2 Answers
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The events of Job 1 say "in that same hour", so that chapter appears to have occurred at the same time. Job 2 occurs at the next meeting between God and the Accuser, but there is no mention of the frequency with which those occurred. But, Job 2 says:

And they sat with him on the ground seven days and seven nights, and no one spoke a word to him, for they saw that his suffering was very great.

There is nothing in the text to indicate anything other than nine speeches one after the other, followed by God's intervention. While there is clearly a gap between Job 1 and 2, really, one can only say "a little more than a week" from the text.

That said, historically, Job has been lumped not with the historical books, but rather with the Ketuvim- the "writings." Unlike say, Judges, Job has no historical dating, and does not make any claim to be a record of things that actually occurred. (And please note: I read the Bible very literally!) And, given its position in the literary section of the Bible, it is thus under no compunction to be a record of actual events. Some scholars place Job very early in ancient history.

As there is no tie to any events, it is impossible to say anything beyond the events mentioned in the book. The series of speeches would indicate some time, but beyond that, it would be like asking how long Romeo had been asleep when Juliet had her little drinking problem.

In the the Zohar (Kabbalah) Pinchas page 231a the meetings between God and the accuser are said to have taken place on the Day of Judgement, which is the Jewish new year, which would mean the meetings were every year.

Rabbi Yehuda said to Rabbi Shimon, Let my master say some beautiful [secret] things about Rosh Hashanah. Rabbi Shimon opened by quoting: "there was (in Hebrew, 'vayehi') the day." (Job 1:6) Wherever it is written: 'vayehi', it refers to a situation of distress. "Now it was in the days of" also refers to distress. Certainly "Now there was the day" refers to a day on which there is distress and this is [referring to] Rosh Hashanah [the Day of Judgment], a day on which harsh judgment is on the world.